U.S. patent application number 10/442089 was filed with the patent office on 2003-12-04 for process for the recovery of phenol and biphenols.
This patent application is currently assigned to POLIMERI EUROPA S.p.A.. Invention is credited to Bianchi, Daniele, Bortolo, Rossella, Carnelli, Lino, Moscotti, Daniele.
Application Number | 20030221948 10/442089 |
Document ID | / |
Family ID | 11450018 |
Filed Date | 2003-12-04 |
United States Patent
Application |
20030221948 |
Kind Code |
A1 |
Bortolo, Rossella ; et
al. |
December 4, 2003 |
PROCESS FOR THE RECOVERY OF PHENOL AND BIPHENOLS
Abstract
A process is described for the recovery of phenol and biphenols
from their homogeneous mixtures containing benzene, sulfolane and
water, which is based on the use of an alkaline solution and
benzene for the separation of biphenols from sulfolane, after
removing the benzene, H.sub.2O and phenol contained in the reaction
effluent. The process allows the recovery of phenol and biphenol
by-products dissolved in sulfolane, directly obtaining the purified
solvent containing the benzene necessary for the feeding to the
reactor for the direct oxidation of benzene, as well as the
biphenols dissolved in water and pure phenol.
Inventors: |
Bortolo, Rossella; (Novara,
IT) ; Carnelli, Lino; (Carbonate, IT) ;
Moscotti, Daniele; (Brugherio, IT) ; Bianchi,
Daniele; (Arese, IT) |
Correspondence
Address: |
OBLON, SPIVAK, MCCLELLAND, MAIER & NEUSTADT, P.C.
1940 DUKE STREET
ALEXANDRIA
VA
22314
US
|
Assignee: |
POLIMERI EUROPA S.p.A.
Brindisi
IT
|
Family ID: |
11450018 |
Appl. No.: |
10/442089 |
Filed: |
May 21, 2003 |
Current U.S.
Class: |
203/43 ;
568/750 |
Current CPC
Class: |
C07C 37/86 20130101;
C07C 37/685 20130101; C07C 37/78 20130101; C07C 37/74 20130101;
Y02P 20/582 20151101; C07C 37/72 20130101; C07C 37/78 20130101;
C07C 39/04 20130101; C07C 37/78 20130101; C07C 39/15 20130101; C07C
37/86 20130101; C07C 39/04 20130101; C07C 37/86 20130101; C07C
39/15 20130101; C07C 37/72 20130101; C07C 39/235 20130101; C07C
37/74 20130101; C07C 39/235 20130101; C07C 37/72 20130101; C07C
39/15 20130101; C07C 37/72 20130101; C07C 39/04 20130101; C07C
37/685 20130101; C07C 39/04 20130101; C07C 37/685 20130101; C07C
39/15 20130101 |
Class at
Publication: |
203/43 ;
568/750 |
International
Class: |
C07C 037/80 |
Foreign Application Data
Date |
Code |
Application Number |
May 31, 2002 |
IT |
MI2002A 001187 |
Claims
1. A process for the recovery of phenol and biphenols from their
homogeneous mixtures containing benzene, sulfolane and water, which
comprises the following steps: (a) feeding the reaction mixture
containing benzene, water, phenol, sulfolane and reaction
by-products (biphenols), to a distillation unit consisting of two
or more columns, to obtain one or more products at the head,
essentially consisting of the benzene-water azeotropic mixture and
phenol, and a product at the bottom, consisting of sulfolane,
phenol and reaction by-products; (b) feeding the benzene-water
azeotropic mixture to a condensation system consisting of one or
more condensers in series in which, after de-mixing, an aqueous and
a benzene phase are separated, the latter being partially sent back
to the distillation unit as reflux, whereas the aqueous phase is
totally collected; (c) feeding the bottom product coming from the
distillation unit of step (a), a basic water solution and benzene
to a mixer/separator to effect the salification of the phenols and
obtain the de-mixing of the system into an organic phase consisting
of benzene and sulfolane and an aqueous phase consisting of water,
phenol salts and a part of sulfolane; (d) feeding the aqueous phase
coming from the mixer/phase separator (D311) and benzene to a
liquid/liquid extraction column (C310) to obtain, at the head, an
organic extract saturated with water containing benzene and
sulfolane and, at the bottom, a refined product containing the
phenol salts in a water solution; (e) feeding the organic phases
coming from the steps (c) and (d) and water to a mixing/de-mixing
system (D312) to obtain, at the head, an organic stream containing
sulfolane, benzene and water and an aqueous stream, saturated with
organic products, which is sent to the extraction column C310; (f)
feeding the organic phase coming from step (e) to a distillation
column C320 in which the heterogeneous benzene-water azeotropic
mixture with the highest pressure separates at the head, and a
product consisting of sulfolane, benzene and water separates at the
bottom; (g) feeding the azeotropic mixture obtained in step (f) to
a condensation system consisting of one or more condensers in which
an aqueous phase is separated and is completely removed and used
for preparing the basic aqueous solution to be adopted for the
salification of phenols and also a benzene phase which is sent back
to the column as reflux; (h) feeding the refined product leaving
the extraction column C310 to a mixer and acidifying with an
inorganic acid or CO.sub.2 to release the phenols from their salts;
(i) feeding the aqueous saline solution obtained in step (h) and an
extracting agent to an extraction column C410 to obtain an extract
containing biphenols, at the head, and a refined product consisting
of saline water, at the bottom; (l) feeding the refined product to
a distillation column C430 to obtain the residual extracting agent
together with water, at the head, and the saline solution, at the
bottom, which is sent for disposal or recovery; (m) feeding the
extract coming from the column C410 and the head product of column
C430 to a distillation column C420 obtaining the heterogeneous
azeotropic mixture of H.sub.2O-extraction solvent at the head, and
a solution containing water and biphenols at the bottom; (n)
feeding the head product to a condensation system consisting of one
or more condensers in which an aqueous phase is obtained which is
sent as reflux to the column C420 of step (m) and an organic phase
containing the extracting agent; (o) feeding a portion of the
organic phase coming from the condenser to a distillation column
C440 to obtain a benzene-water mixture at the head, which is
recycled to step (a) and the extracting agent at the bottom, which
is fed directly to the separation column C410.
2. The process according to claim 1, wherein in step (a) the
distillation unit consists of three columns C210, C220 and C230
operating at a temperature at the bottom ranging from 150 to
200.degree. C. and at different pressures and temperatures at the
head.
3. The process according to claim 2, wherein the column C210
operates at a pressure ranging from 0.1 to 0.9 bar and a
temperature at the head ranging from 20 to 100.degree. C.
4. The process according to claim 2, wherein the column C220
operates at a pressure ranging from 0.05 to 0.1 bar and a
temperature at the head ranging from 30 and 100.degree. C.
5. The process according to claim 2, wherein the column C230
operates at a pressure ranging from 0.01 to 0.1 bar and a
temperature at the head ranging from 30 to 90.degree. C.
6. The process according to claim 1, wherein in step (c) the basic
solution is selected from NaOH, KOH, Na.sub.2CO.sub.3,
K.sub.2CO.sub.3, Na.sub.3PO.sub.4 and K.sub.3PO.sub.4.
7. The process according to claim 1, wherein the acidifying medium
in the step (h) is an inorganic acid or CO.sub.2.
8. The process according to claim 1, wherein in step (i) the
extracting agent is selected from aromatic hydrocarbons, alcohols,
ketones, esters or ethers insoluble or partially soluble in water,
particularly cumene, benzene, tert-amyl alcohol, isopropyl ether,
3-pentanone, diisopropyl ketone, butyl acetate, methyl isobutyl
ketone.
9. The process according to claim 8, wherein the extracting agent
is methyl isobutyl ketone.
Description
[0001] The present invention relates to a process for the recovery
of phenol and biphenol by-products from solutions containing
them.
[0002] In particular, the present invention relates to a process
for the recovery of phenol and biphenol by-products from their
homogeneous mixtures containing benzene, sulfolane and water.
[0003] Phenol is a useful product in the preparation of synthetic
resins, insecticides and antioxidants.
[0004] In industry, phenol is normally prepared by means of benzene
alkylation with propylene to give isopropyl benzene, oxidation to
the corresponding tert-hydroperoxide and subsequent cleavage to
phenol and acetone in the presence of an acid catalyst.
[0005] The reaction mixture, after neutralization of the residual
acid, is subjected to a series of subsequent distillations for the
separation of products and by-products from the non-converted
reagents which are recycled to the reaction.
[0006] A process has recently been proposed for the production of
phenol by means of the direct oxidation of benzene with hydrogen
peroxide, in the presence of titanium silicalite, which operates in
liquid phase in the presence of sulfolane, as reaction solvent
(U.S. Pat. No. 6,133,487).
[0007] The process which allows the oxidation of benzene to phenol
to be obtained with high yields, is always accompanied by
subsequent reactions which lead to the formation poly-hydroxylated
products (mainly biphenols), in concentrations varying according to
the reaction conditions.
[0008] The reaction effluent consequently contains the sulfolane
solvent, non-converted benzene, the water formed and that
introduced with the diluted hydrogen peroxide, in addition to the
phenol, biphenols and tars produced.
[0009] In this case, the application of the traditional
purification process, which includes the sequential distillation of
the various components, is not suitable as, after the separation of
the most volatile products (benzene, water and phenol), the
distillation of the sulfolane would be required for removing the
by-products having a higher boiling point than the solvent.
[0010] This solution, in addition to being uneconomical, does not
allow the separation of the biphenols --such as catechol, for
example--which together with sulfolane form an azeotropic mixture
with the highest temperature.
[0011] In the present case, it is not even possible to resort to
simple extraction with soda in water solution (U.S. Pat. No.
5,338,453), as sulfolane is miscible with water in all
proportions.
[0012] It has now been found that it is possible to overcome the
above-mentioned drawbacks of the known technique by means of the
process of the present invention which is based on the use of an
alkaline solution and benzene for the separation of biphenols from
sulfolane, after the removal of the benzene, H.sub.2O and phenol
contained in the reaction effluent.
[0013] The process of the present invention allows the recovery of
the biphenol by-products dissolved in sulfolane, directly obtaining
the purified solvent containing the benzene necessary for the
feeding to the reactor for the direct oxidation of benzene, in
addition to biphenols dissolved in water and pure phenol.
[0014] In accordance with the above, an objective of the present
invention is a process for the recovery of phenol and biphenols
from their homogeneous mixtures containing benzene, sulfolane and
water, which comprises the following steps:
[0015] (a) feeding the reaction mixture containing benzene, water,
phenol, sulfolane and the reaction by-products (biphenols), to a
distillation unit consisting of two or more columns, to obtain one
or more products at the head, essentially consisting of the
benzene-water azeotropic mixture and phenol, and a product at the
bottom, consisting of sulfolane, residual phenol and reaction
by-products;
[0016] (b) feeding the benzene-water azeotropic mixture to a
condensation system consisting of one or more condensers in series
in which, after de-mixing, an aqueous phase and a benzene phase are
separated. The latter is partially sent back to the distillation
unit as reflux, whereas the aqueous phase is totally collected;
[0017] (c) feeding the bottom product coming from the distillation
unit of step (a), a basic water solution and benzene to one or more
mixers and separators (D311) to effect the salification of the
biphenols in order to obtain the den mixing of the system into an
organic phase consisting of benzene and sulfolane and an aqueous
phase consisting of water, biphenol salts and a part of
sulfolane;
[0018] (d) feeding the aqueous phase coming from the
mixer/separator (D311) and benzene to a liquid/liquid extraction
column (C310) to obtain, at the head, an organic extract saturated
with water containing benzene and sulfolane and, at the bottom, a
refined product containing phenol salts in water solution;
[0019] (e) feeding the organic phases coming from steps (c) and
[0020] (d) and water to a mixing/de-mixing system (D312) to obtain
an organic stream containing sulfolane, benzene and water and an
aqueous stream, saturated with organic products, which is sent to
the extraction column C310;
[0021] (f) feeding the organic phase coming from step (e) to a
distillation column C320 wherein the heterogeneous benzene-water
azeotropic mixture with the highest pressure separates at the head,
and a product consisting of sulfolane, benzene and residual water
separates at the bottom;
[0022] (g) feeding the azeotropic mixture obtained in step (f) to a
condensation system consisting of one or more condensers wherein an
aqueous phase separates and is completely removed and used for
preparing the basic aqueous solution to be adopted for the
salification of phenols and a benzene phase which is sent back to
the column as reflux;
[0023] (h) feeding the refined product leaving the extraction
column C310 to a mixer and acidifying with an inorganic acid or
CO.sub.2 to release phenols from their salts;
[0024] (i) feeding the aqueous saline solution obtained in step (h)
and an extracting agent to an extraction column C410 to obtain an
extract containing biphenols, at the head, and a refined product
consisting of saline water containing residues of the extracting
agent, at the bottom;
[0025] (l) feeding the refined product to a distillation column
C430 to obtain the residual extracting agent together with water,
at the head, and the saline solution, at the bottom, which is sent
for disposal or recovery;
[0026] (m) feeding the extract leaving the column C410 and the head
product of column C430 to a distillation column C420, obtaining the
heterogeneous H.sub.2O-extraction solvent azeotropic mixture at the
head and a solution containing water and biphenols at the
bottom;
[0027] (n) feeding the head product to a condensation system
consisting of one or more condensers wherein an aqueous phase is
obtained which is sent as reflux to column C420 of step (m)
together with an organic phase containing the extracting agent;
[0028] (o) feeding a portion of the organic phase coming from the
condenser to a distillation column C440 to obtain a benzene-water
mixture at the head, which is recycled to step (a) and the
extracting agent at the bottom, which is directly fed to the
separation column C410.
[0029] According to an embodiment of the present invention, the
process comprises:
[0030] (a) feeding the reaction mixture containing benzene, water,
phenol, sulfolane and reaction by-products to a first distillation
column C210 to obtain product at the head, consisting of the
benzene-water azeotropic mixture and a product at the bottom,
including the residual benzene and water, sulfolane, phenol and
by-products;
[0031] (b) feeding the benzene-water azeotropic mixture to a
condensation system consisting of one or more condensers in series
in which, after de-mixing, an aqueous and a benzene phase are
separated. The latter is partially sent back to the distillation
column as reflux, whereas the aqueous phase is totally
collected;
[0032] (c) feeding the bottom product leaving the column C210 to a
second distillation column C220, to obtain a head
product--containing benzene, water and traces of phenol--which is
recycled to step (a), and a tail product consisting of phenol,
sulfolane and biphenols;
[0033] (d) feeding the tail product coming from the distillation
column C220 to a third distillation column C230, to obtain pure
phenol as a side cut, a distilled product at the head containing
possible light products (benzene and water) and an effluent, at the
tail, consisting of sulfolane containing residues of phenol and
biphenols;
[0034] (e) feeding the tail effluent leaving column C230, a basic
water solution and benzene to one or more mixers/separators (D311)
to obtain the salification of the phenols, feeding benzene in such
a quantity as to cause the de-mixing of the system into an organic
phase consisting of sulfolane and benzene and an aqueous solution
containing the phenol salts and a portion of sulfolane;
[0035] (f) feeding the aqueous phase leaving the mixer/separator
(D311) and benzene to a liquid/liquid extraction column (C310) to
obtain, at the head, an organic extract saturated with water
containing benzene and sulfolane and, at the bottom, a refined
product containing phenol salts in water solution;
[0036] (g) feeding the organic phases coming from steps (e) and (f)
and water to a mixing/de-mixing system (D312) to obtain an organic
stream containing sulfolane, benzene and water and an aqueous
stream, saturated with organic products, which is sent to the
extraction column C310;
[0037] (h) feeding the organic phase coming from step (g) to a
distillation column C320 in which the heterogeneous benzene-water
azeotropic mixture with the highest pressure separates at the head,
and a product consisting of sulfolane, benzene and residual water
separates at the bottom;
[0038] (i) feeding the azeotropic mixture obtained in step (h) to a
condensation system consisting of one or more condensers wherein an
aqueous phase is separated and is completely removed and used for
preparing the basic aqueous solution to be adopted for the
salification of phenols together with a benzene phase which is sent
back to the column as reflux;
[0039] (l) feeding the refined product leaving the extraction
column C310 to a mixer and acidifying with an organic acid or
CO.sub.2 to release phenols from their salts;
[0040] (m) feeding the aqueous saline solution obtained in step (l)
and an extracting agent to an extraction column C410 to obtain an
extract containing biphenols, at the head, and a refined product
consisting of saline waters, at the bottom;
[0041] (n) feeding the refined product to a distillation column
C430 to obtain the residual extracting agent together with water,
at the head, and the saline solution, at the bottom, which is sent
for disposal or recovery;
[0042] (o) feeding the extract coming from column C410 and the head
product of column C430 to a distillation column C420 obtaining the
heterogeneous H.sub.2O-extraction solvent azeotropic mixture at the
head and a solution containing water and biphenols at the
bottom;
[0043] (p) feeding the head product to a condensation system
consisting of one or more condensers in which an aqueous phase is
obtained, which is sent as reflux to column C420 of step (o),
together with an organic phase containing the extracting agent;
[0044] (q) feeding a portion of the organic phase coming from the
condenser to a distillation column C440 to obtain a benzene-water
mixture at the head, which is recycled to step (a) and the
extracting agent at the bottom, which is directly fed to the
separation column C410.
[0045] According to an embodiment of the process of the present
invention, the reaction effluent, before being fed to the
distillation unit, can be subjected to degassing in a flash (D210)
in order to remove most of the dissolved inert gases.
[0046] The flash operates at a temperature ranging from 20 to
100.degree. C. and at a pressure of between 0.1 and 0.9 bar,
preferably at a temperature ranging from 40 to 70.degree. C. and a
pressure of between 0.4 and 0.7 bar.
[0047] The stream coming from flash is subsequently fed to the
distillation system.
[0048] The columns C210, C220 and C230 operate under substantially
identical temperature conditions at the bottom, i.e. at about
150-200.degree. C., but at different pressures and temperatures at
the head.
[0049] In particular, the column C210 operates at a pressure
ranging from 0.1 to 0.9 bar and a temperature at the head ranging
from 20 to 100.degree. C., the column C220 operates at a pressure
ranging from 0.5 to 0.1 bar and a temperature at the head ranging
from 30 to 100.degree. C., whereas the column C230 operates at a
pressure ranging from 0.01 to 0.1 bar and a temperature at the head
ranging from 30 to 90.degree. C.
[0050] The column C210 has the function of separating benzene and
H.sub.2O at the head. The condensed product, after demixing, is
separated into aqueous and benzene phases. The latter is partially
sent back to the column as reflux, whereas the aqueous phase is
totally collected.
[0051] The tail effluent of the column contains residual benzene
and H.sub.2O, to avoid an excessive temperature increase in the
boiler.
[0052] The exhaustion of the residual benzene and H.sub.2O
contained in the tail stream of C210 is effected in a second column
(C220), operating at a lower pressure with respect to the preceding
one, of which the distillate, also containing phenol, is recycled
to C210.
[0053] The tail residue of column C220 is sent to a subsequent
distillation column (C230) in which pure phenol is obtained as a
side cut at the 6.sup.th step, whereas any possible light products
still present are concentrated in the distillate at the head and
are recycled to C210.
[0054] The tail effluent of C230, consisting of sulfolane
containing residual phenol and biphenols, is sent to the biphenol
separation section, in which it is first treated with an excess of
a basic aqueous solution to salify the phenols present. A solution
of NaOH, KOH, Na.sub.2CO.sub.3, K.sub.2CO.sub.3, Na.sub.3PO.sub.4,
K.sub.3PO.sub.4 is normally used. An NaOH solution is preferably
adopted.
[0055] Mixing with benzene is subsequently effected, in an amount
suitable for causing the de-mixing of the system into an aqueous
phase containing the alkaline salts of phenols and a part of
sulfolane, and an organic phase consisting of sulfolane and benzene
saturated with water.
[0056] After separation, the aqueous phase is sent to a
liquid-liquid extraction column (C310), where it is treated with
benzene to extract the sulfolane contained therein, thus obtaining
an extracted product saturated with water, consisting of benzene
and sulfolane, and a refined product containing alkaline phenates
in water solution.
[0057] Part of the extraction solvent comes from the head of C210,
the rest consists of the feeding of fresh benzene to reintegrate
the amount consumed in the reaction.
[0058] The organic phases coming from D311 and C310 are first
washed with H.sub.2O in D312 to remove any possible traces of salts
contained in the dispersed H.sub.2O, and sent to a distillation
column (C320) to separate the excess water. The operation is
effected by separating the heterogeneous benzene-H.sub.2O
azeotropic mixture with the highest pressure at the head.
[0059] After de-mixing, the condensate is separated into aqueous
and benzene phases. The latter is entirely sent back to the column
as reflux, whereas the aqueous phase is totally collected and
re-used for the preparation of the alkaline solution to be used for
the salification.
[0060] The tail effluent of the column (C320) consists of
sulfolane, benzene and H.sub.2O in concentrations suitable for
recycling the mixture to the reaction.
[0061] The refined product, containing sodium phenates in water
solution, is fed to a mixer together with an acid, preferably
H.sub.2SO.sub.4, to release phenols from their salts. The sulfate
water solution thus obtained and an extracting agent selected from
aromatic hydrocarbons, alcohols, ketones, esters or ethers
insoluble or partially soluble in water, particularly cumene,
benzene, tert-amyl alcohol, isopropyl ether, 3-pentanone,
diisopropyl ketone, butyl acetate, methyl isobutyl ketone,
preferably methyl isobutyl ketone (MIK), are fed to an extraction
column, producing an extract containing biphenols in the organic
solvent and a refined product consisting of sulfate water saturated
with said solvent.
[0062] The refined product leaving the extraction column is fed to
a distillation column for stripping the residual solvent, obtaining
sulfate water at the tail, which can be sent for disposal.
[0063] A stream of H.sub.2O coming from the head of C210, is also
sent to C430, to favour the stripping of the solvent. The column is
also equipped with a partial condenser, wherein the condensed
product is entirely sent back to the column as reflux.
[0064] The recovery of the extraction solvent is effected by
sending the extract of C410 and the vapours at the head of the
column C430 to the same distillation column (C420), obtaining at
the head the heterogeneous azeotropic mixture of H.sub.2O-solvent
with the highest pressure.
[0065] After condensation, the distillate is separated into organic
and aqueous phases. The latter is entirely sent back to the column
as reflux, whereas the organic phase, consisting of the organic
solvent saturated with water, is recycled to the extraction in
C410.
[0066] Finally, an aqueous solution of biphenols is obtained at the
tail.
[0067] As the organic solvent distilled in C420 contains a small
amount of benzene coming from the previous operations, a part of
the solvent (about 5%) must be subjected to distillation in the
column C440 to allow the removal of the benzene, thus avoiding its
accumulation in the extraction loop.
[0068] In this way, a distillate consisting of benzene and H.sub.2O
is obtained at the head of the column, which is recycled to C210,
whereas the organic solvent devoid of benzene is obtained at the
tail.
[0069] The process of the present invention can be better
understood by referring to the block schemes of FIG. 1, which
represents an illustrative but not limitative embodiment
thereof.
[0070] The following operative example is provided for merely
illustrative and non-limiting purposes.
EXAMPLE 1
[0071] The scheme of FIG. 1 is followed for the recovery of phenol
and biphenols starting from:
[0072] a stream coming from a phenol production plant consisting of
36% by weight of benzene, 2% by weight of water, 4% by weight of
phenol, 0.4% by weight of biphenols and 57.6% by weight of
sulfolane;
[0073] an aqueous solution of NaOH and benzene fed to the
mixers/separators D311 in such a quantity as to obtain the
salification of phenols and cause the de-mixing of the system into
an aqueous phase containing the sodium salts of phenols as well as
part of the sulfolane, and an organic phase consisting of sulfolane
and benzene, respectively;
[0074] a solution containing sulfuric acid at 98% by weight, fed to
a mixer to release phenols from their salts;
[0075] The amounts and data relating to the single streams are
shown in Table 1 below.
1 TABLE 1 NaOH Reactor effluent Phenol produced water solution Flow
rate weight Flow rate weight Flow rate weight Nr. Components kg/h %
kg/h % kg/h % 1 Benzene 230480.031 35.9276 -- -- 87.108 0.2449 2
H.sub.2O 15834.952 2.4684 -- -- 32826.020 92.3046 3 Phenol
25094.779 3.9118 25000.000 100.0000 -- -- 4 Catechol 2150.000
0.3351 -- -- -- -- 5 Hydroquinone 1080.000 0.1684 -- -- -- -- 6
Tars 380.000 0.0592 -- -- -- -- 7 Sulfolane 366443.938 57.1218 --
-- -- -- 8 NaOH -- -- -- -- 2649.585 7.4505 9 H.sub.2SO.sub.4 -- --
-- -- -- -- 10 Na.sub.2SO.sub.4 -- -- -- -- -- -- 11 MIK -- -- --
-- -- -- 12 O.sub.2 12.602 0.0020 -- -- -- -- 13 N.sub.2 36.539
0.0057 -- -- -- -- Flow rate (kg/h) 641512.842 25000.000 35562.713
Phase Liquid Liquid Liquid Temperature (.degree. C.) 106.11 79.41
60.00 Pressure (Atm) 1.500 0.019 1.000 Saline water to Water
solutions H.sub.2SO.sub.4 be disposed of of biphenols Flow rate
weight Flow rate weight Flow rate weight Nr. Components kg/h % kg/h
% kg/h % 1 Benzene -- -- -- -- -- -- 2 H.sub.2O 66,245 2.0000
18043.600 79.3198 9093.807 71.0580 3 Phenol -- -- 0.941 0.0041
93.838 0.7332 4 Catechol -- -- -- -- 2150.000 16.7999 5
Hydroquinone -- -- -- -- 1080.000 8.4390 6 Tars -- -- -- -- 380.000
2.9693 7 Sulfolane -- -- -- -- 0.004 0.0000 8 NaOH -- -- -- -- --
-- 9 H.sub.2SO.sub.4 3245.985 98.0000 -- -- -- -- 10
Na.sub.2SO.sub.4 -- -- 4703.371 20.6761 -- -- 11 MIK -- -- -- --
0.080 0.0006 12 O.sub.2 -- -- -- -- -- -- 13 N.sub.2 -- -- -- -- --
-- Flow rate (kg/h) 3312.230 22747.910 12797.729 Phase Liquid
Liquid Liquid Temperature (.degree. C.) 50.00 109.60 105.43
Pressure (Atm) 1.000 1.350 1.150
* * * * *